This paper centers on Dillon O’Brien, one the seven Irish-born immigrants whom Charles Fanning labels the “Famine Generation” of Irish American writers, and his problematic relationship with Native America. Not long after arrival in the United States, O’Brien was appointed principal of a Catholic Church-sponsored Indian School in an isolated Wisconsin trading post. Several years later, he moved with his family to St. Paul, Minnesota, where he helped the Catholic Colonization Society. The paper includes an analysis of two of his novels set in the American West Dead Broke: A Western Tale (1873) and Widow Melville’s Boarding House (1881) to help determine the extent to which O’Brien’s notions of Irish whiteness was tied to the white supremacist assumptions inherent in John L. O’Sullivan’s notion of Manifest Destiny.